Hydrochloric Acid → 4-(Dimethylamino)piperidine dihydrochloride

HRID 22953

Reaction equation

HRID 22953 reaction equation
[ClH:1].CNC.C(OC(C1CCNC(=O)C1)=O)(C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C(OC([N:39]1[CH2:44][CH2:43][CH:42]([N:45]([CH3:47])[CH3:46])[CH2:41][CH2:40]1)=O)(C)(C)C.Cl>C(N(CC)CC)C.C(Cl)Cl>[ClH:1].[ClH:1].[CH3:46][N:45]([CH3:47])[CH:42]1[CH2:43][CH2:44][NH:39][CH2:40][CH2:41]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10473Dimethylamine, hydrochlorideHCID 2724942TriacetoxyborohydrideHCID 223181614-Boc-piperidinoneHCID 22591376Tert-butyl 4-(dimethylamino)piperidine-1-carboxylate

Product 1

HCID 225914404-(Dimethylamino)piperidine dihydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Dimethylamine hydrochloride (430 mg) was added to a methylene chloride (10 ml) solution containing 4-(tert-butoxycarbonyl)piperidone (1.0 g), and under ice-cooling, triethylamine (0.84 ml) and triacetoxyborohydride (1.17 g) were further added thereto, and the mixture was stirred at room temperature for 3 hours to undergo reaction, thereby obtaining N-tert-butoxycarbonyl-4-dimethylaminopiperidine. This compound was acid-treated with hydrochloric acid to obtain 4-(dimethylamino)piperidine.dihydrochloride.

Workup

  1. temperatureunder ice-cooling
  2. customreaction

Sources & evidence

ORD record
ord-2a621ec232ee49fcbfb7856de2c1ed48
Source dataset
uspto-grants-2005_02
Patent number
US06849622B2

Linked notes

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